Kinetic Resolution of a Planar-Chiral [2.2]Paracyclophane Derivative by Helical-Peptide-Catalyzed Michael Addition of Nitromethane
Kinetic Resolution of a Planar-Chiral [2.2]Paracyclophane Derivative by Helical-Peptide-Catalyzed Michael Addition of Nitromethane
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DOI：
10.1002/ejoc.201500594
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发表时间：
2015-08-01
影响因子：
2.8
通讯作者：
Kudo, Kazuaki
中科院分区：
文献类型：
--
作者：
Akagawa, Kengo;Nishi, Nobuhiro;Kudo, Kazuaki
通过在对环烷结构上的烯酮取代基上Michael加成硝基甲烷，开发了一种树脂支撑的肽催化剂，用于平面手性[2.2]对环烷衍生物的动力学拆分。螺旋基肽可以有效地区分[2.2]副环环烷结构的平面手性，并优先将一种对映体转化为Michael加合物。通过优化螺旋链n端的肽序列，获得了高度的对映选择性。
A resin-supported peptide catalyst was developed for kinetic resolution of a planar-chiral [2.2]paracyclophane derivative through Michael addition of nitromethane to an enone substituent on the paracyclophane structure. A helix-based peptide was effective to discriminate the planar chirality of the [2.2]paracyclophane structure, and to convert one enantiomer preferentially into the Michael adduct. By optimizing the peptide sequence at the N-terminus of the helical chain, highly enantioselective resolution was attained.